title: Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.
abstract: Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at -78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330, USA. thomas.minehan@csun.edu.
authors.forename: Aaron
authors.initials: A
authors.lastname: Christopher
authors.forename: Dahniel
authors.initials: D
authors.lastname: Brandes
authors.forename: Stephen
authors.initials: S
authors.lastname: Kelly
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan
mesh_terms: D003080:Cold Temperature; D004987:Ethers / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D004987:Ethers; D007783:Lactones; D009942:Organometallic Compounds; C434823:n-butyllithium